2-Cyclohexylethanol → 4-(2-Cyclohexylethoxy)-3-oxobutanoic acid 3,3-diphenylpropyl ester

HRID 1297029Notes

Reaction equation

HRID 1297029 reaction equation
[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:8][CH2:9][O:10][C:11](=[O:17])[CH2:12][C:13]([CH2:15]Cl)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH:26]1([CH2:32][CH2:33][OH:34])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>C1COCC1>[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:8][CH2:9][O:10][C:11](=[O:17])[CH2:12][C:13](=[O:14])[CH2:15][O:34][CH2:33][CH2:32][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 205082-CyclohexylethanolHCID 24758Sodium hydride2×HCID 86760519(3,3-Diphenylpropane-1-yl)4-chloroacetoacetate

Product 1

HCID 690630434-(2-Cyclohexylethoxy)-3-oxobutanoic acid 3,3-diphenylpropyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

2.5 ml of a solution of 610 mg (1.84 mmol) of (3,3-diphenylpropane-1-yl)4-chloroacetoacetate in THF was added dropwise to a suspension of 158 mg (3.95 mmol) of sodium hydride (60% oily) in 5 ml of THF at 0° C., and they were stirred at room temperature for 20 minutes. An alkoxide solution previously prepared by adding 397 mg (3.09 mmol) of 2-cyclohexylethanol to 5 ml of a solution of 134 mg (3.36 mmol) of sodium hydride (60% oily) in THF was added to the obtained mixture at 0° C., and they were stirred at room temperature for 3 nights. THF was evaporated under reduced pressure. Water was added to the residue. The obtained mixture was washed with ethyl acetate. The aqueous layer was acidified with 2 N hydrochloric acid. After the extraction with ethyl acetate followed by drying over sodium sulfate, ethyl acetate was evaporated under reduced pressure to obtain the title compound.

Workup

  1. additionwas added to the obtained mixture at 0° C.
  2. stirringthey were stirred at room temperature for 3 nights
  3. customTHF was evaporated under reduced pressure
  4. additionWater was added to the residue
  5. washThe obtained mixture was washed with ethyl acetate
  6. extractionAfter the extraction with ethyl acetate
  7. dry with materialby drying over sodium sulfate, ethyl acetate
  8. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-86a48be183084c18a17b8d321fd2ebcb
Source dataset
uspto-grants-2007_07
Patent number
US07247645B2

Reaction notes

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